2,4-二氯苄醇 | 1777-82-8

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醇
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-二氯苄醇
• 中文别名: 2,4-二氯苯甲醇；二氯苯甲醇
• 英文名称: (2,4-dichlorophenyl)methanol
• 英文别名: 2,4-dichlorobenzyl alcohol
• CAS: 1777-82-8
• 化学式: C₇H₆Cl₂O
• mdl: MFCD00004606
• 分子量: 177.03
• InChiKey: DBHODFSFBXJZNY-UHFFFAOYSA-N

物化性质

• 熔点：
  55-58 °C(lit.)
• 沸点：
  150 °C (25 mmHg)
• 密度：
  1.2970 (rough estimate)
• 闪点：
  >230 °F
• 溶解度：
  1g/l
• LogP：
  2.8 at 24℃
• 稳定性/保质期：

  常温常压下稳定

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

二氯苯甲醇在肝脏中被代谢，形成马尿酸。

Dichlorobenzyl alcohol is metabolized in the liver to form hippuric acid.

来源:DrugBank

毒理性

• 蛋白质结合

这个药代动力学特性还没有被完全研究。

This pharmacokinetic property has not been fully studied.

来源:DrugBank

吸收、分配和排泄

• 吸收

二氯苯甲醇几乎立即从其配方中释放出来，并在3-4分钟后达到峰值浓度。120分钟后唾液中的浓度大约是给药剂量的50%。

Dichlorobenzyl alcohol is released almost immediately from its formulation and reaches peak concentration after 3-4 minutes. The concentration in saliva after 120 minutes represents about 50% of the administered dose.

来源:DrugBank

吸收、分配和排泄

• 消除途径

在临床前试验中，二氯苯甲醇的皮肤给药导致给药剂量的90%通过肾脏排出。经过代谢后，二氯苯甲醇通过尿液排出。

In preclinical trials, dermal administration of dichlorobenzyl alcohol results in renal elimination of 90% of the administered dose. After metabolism, dichlorobenzyl alcohol is excreted in the urine.

来源:DrugBank

吸收、分配和排泄

• 分布容积

这个药代动力学特性尚未被充分研究。

This pharmacokinetic property has not been fully studied.

来源:DrugBank

吸收、分配和排泄

• 清除

这个药代动力学特性还没有被完全研究。

This pharmacokinetic property has not been fully studied.

来源:DrugBank

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• 海关编码：
  29062900
• RTECS号：
  DO0890000
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  将严密密封容器储存，并存放在阴凉干燥处。

SDS

Name:	2 4-Dichlorobenzyl Alcohol 99% Material Safety Data Sheet
Synonym:	Dybenal(R
CAS:	1777-82-8

Section 1 - Chemical Product MSDS Name:2 4-Dichlorobenzyl Alcohol 99% Material Safety Data Sheet
Synonym:Dybenal(R

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1777-82-8	2,4-Dichlorobenzyl Alcohol	99%	217-210-5

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1777-82-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white - light yellow
Odor: characteristic odor - faint odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 150 deg C @ 25.00mm Hg
Freezing/Melting Point: 55 - 58 deg C
Autoignition Temperature: Not applicable.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: IN WATER: 0.1% (20C)
Specific Gravity/Density:
Molecular Formula: C7H6Cl2O
Molecular Weight: 177.03

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1777-82-8: DO0890000 LD50/LC50:
CAS# 1777-82-8: Oral, mouse: LD50 = 2300 mg/kg.
Carcinogenicity:
2,4-Dichlorobenzyl Alcohol - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1777-82-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1777-82-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1777-82-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

2,4-二氯苄醇是一种有机中间体，可以通过两种主要途径制备：一是由2,4-二氯苯甲腈经酸解生成2,4-二氯苯甲酸后再还原得到；二是通过2,4-二氯苄基氯的水解直接获得。

制备 第一步

首先合成2,4-二氯苯甲酸。在100 mL圆底烧瓶中，加入2,4-二氯苯甲腈(17.2 g, 0.1 mol)，滴加硫酸(9.8 g, 0.1 mol)溶液。完成滴加后，在125-130℃下保温反应2小时。随后冷却至100℃以下，用水稀释并冷却到50℃以下，进行分层以除去未反应的原料。通过减压脱水浓缩，并在冷却条件下析晶，最终得到2,4-二氯苯甲酸17.38 g，产率为91%。

第二步

接下来合成2,4-二氯苄醇。在100 mL圆底烧瓶中加入2,4-二氯苯甲酸(19.1 g, 0.1 mol)和乙醇(30 mL)，然后在0℃下缓慢滴加NaBH₄(1.9 g, 0.05 mol)与烯碱（质量浓度为2%的氢氧化钠溶液，共10 mL）的混合液。完成滴加并搅拌反应1小时后进行过滤，并用乙醇润洗滤渣三次（每次5 mL）。最终通过蒸馏得到2,4-二氯苄醇15.05 g，产率为85%。

生物活性

2,4-Dichlorobenzyl alcohol是一种温和的防腐剂，能够有效杀死与口喉感染相关的细菌和病毒。

用途

用作医药中间体。

反应信息

• 作为反应物：
  描述：

  2,4-二氯苄醇 在 盐酸 、 potassium dihydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.09h， 生成 2-(2,4-Dichloro-benzylsulfanylmethyl)-2-hydroxy-succinic acid
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  2-((2,4-dichlorobenzyl)oxy)tetrahydro-2H-pyran 在 1,4-diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe₃O₄ nanoparticles 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到2,4-二氯苄醇
  参考文献：
  名称：

  磁性纳米粒子支持DABCO溴化：为喹唑啉酮类和苯并咪唑和羟基的保护/脱保护合成的多功能纳米催化剂†

  摘要：

  发现一种新型的非均相三溴化物类型化合物，负载在磁性Fe 3 O 4纳米颗粒上的1,4-二氮杂双环[2.2.2]辛烷三溴化物（MNPs-DABCO三溴化物）是一种高效且可重复使用的纳米催化剂，可用于一锅法合成2通过分别用2-氨基苯甲酰胺和1,2-苯二胺对醛进行氧化环化反应，制得-芳基喹唑啉-4（3 H）-ones和2-芳基-1 H-苯并[ d ]咪唑。而且，MNPs-DABCO三溴化物通过在室温下改变溶剂介质，催化了多种醇和酚的三甲基甲硅烷基化/四氢吡喃基化和甲硅烷基化/脱吡喃基化。

  DOI：

  10.1039/c7nj00479f

文献信息

• H₅IO₆/KI: A New Combination Reagent for Iodination of Aromatic Amines, and Trimethylsilylation of Alcohols and Phenols through<i>in situ</i>Generation of Iodine under Mild Conditions
  作者：Mohammad Ali Zolfigol、Ardeshir Khazaei、Eskandar Kolvari、Nadiya Koukabi、Hamid Soltani、Maryam Behjunia

  DOI：10.1002/hlca.200900259

  日期：2010.3

  A simple method for the in situ generation of iodine using H5IO6/KI has been developed, and its application in silylation of OH group and iodination of aromatic amines is described.

  已开发出一种使用H 5 IO 6 / KI原位生成碘的简单方法，并描述了其在OH基甲硅烷基化和芳族胺碘化中的应用。
• [EN] PHENOTHIAZINE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE PHÉNOTHIAZINE ET LEURS UTILISATIONS
  申请人：CAMP4 THERAPEUTICS CORP

  公开号：WO2019195789A1

  公开（公告）日：2019-10-10

  The present invention provides phenothiazine compounds, processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment of various diseases or conditions, for example ribosomal disorders and ribosomopathies, e.g. Diamond Blackfan anemia (DBA).

  本发明提供了吩噻嗪化合物，其制备方法，包含该化合物的药物组合物，以及在治疗各种疾病或症状中使用该化合物或组合物，例如核糖体紊乱和核糖体病，例如钻石-布莱克范贫血（DBA）。
• POLYETHYLENE GLYCOL DERIVATIVES OF PALMITOYLETHANOLAMIDE AND ANALOGOUS ACYLETHANOLAMIDES
  申请人：EPITECH GROUP S.r.l.

  公开号：US20150157733A1

  公开（公告）日：2015-06-11

  The synthesis of a series of Polyethylene glycol conjugates (esters and carbonates) of PEA and its analogous acylethanolamides, have higher water solubility and good hydrophilic/lipophilic balance, resulting in (i) improved accumulation in tissues (particularly skin and mucosae), (ii) prolonged release, and (iii) increased bioavailability. Improvement of PEA and analogous acylethanolamides levels in the tissues—particularly in the skin and mucosae—and their prolonged release is due to the improved bioavailability of related conjugates. Conjugates are able to extend the time frame in which PEA and analogous acylethanolamides exert their pharmacological effects.

  一系列聚乙二醇酯和碳酸酯的PEA及其类似的酰乙醇胺共轭物具有更高的水溶性和良好的亲水/疏水平衡，导致（i）在组织中（特别是皮肤和粘膜）的积累增加，（ii）释放延长，以及（iii）生物利用度增加。PEA和类似的酰乙醇胺在组织中（特别是皮肤和粘膜）的水平提高以及它们的延长释放是由于相关共轭物生物利用度的提高。共轭物能够延长PEA和类似的酰乙醇胺发挥药理效应的时间范围。
• SBA-15-Functionalized 3-Oxo-ABNO as Recyclable Catalyst for Aerobic Oxidation of Alcohols under Metal-Free Conditions
  作者：Babak Karimi、Elham Farhangi、Hojatollah Vali、Saleh Vahdati

  DOI：10.1002/cssc.201402059

  日期：2014.9

  The nitroxyl radical 3‐oxo‐9‐azabicyclo [3.3.1]nonane‐N‐oxyl (3‐oxo‐ABNO) has been prepared using a simple protocol. This organocatalyst is found to be an efficient catalyst for the aerobic oxidation of a wide variety of alcohols under metal‐free conditions. In addition, the preparation and characterization of a supported version of 3‐oxo‐ABNO on ordered mesoporous silica SBA‐15 (SABNO) is described

  硝酰基自由基3-氧代-9-氮杂双环[3.3.1]壬烷-N-oxyl（3-oxo-ABNO）已使用简单的方案制备。已发现这种有机催化剂是在无金属条件下对多种醇进行好氧氧化的有效催化剂。此外，首次描述了在有序介孔二氧化硅SBA-15（SABNO）上支持的3-氧代ABNO的制备和表征。使用多种技术对催化剂进行了表征，包括同时热分析（STA），透射电子显微镜（TEM）和氮吸附分析。与（2,2,6,6-四甲基哌啶-1-基）氧基（TEMPO）相比，该催化剂在相同条件下几乎可以对相同范围的醇进行好氧氧化，其催化性能与其均相类似物相当，并且催化活性要好得多。反应条件。
• Aerobic Oxidation of Alcohols Catalyzed by <i>in Situ</i> Generated Gold Nanoparticles inside the Channels of Periodic Mesoporous Organosilica with Ionic Liquid Framework
  作者：Babak Karimi、Akram Bigdeli、Ali Asghar Safari、Mojtaba Khorasani、Hojatollah Vali、Somaiyeh Khodadadi Karimvand

  DOI：10.1021/acscombsci.9b00160

  日期：2020.2.10

  In situ generated gold nanoparticles inside the nanospaces of periodic mesoporous organosilica with an imidazolium framework ([email protected]) were found to be highly active, selective, and reusable catalysts for the aerobic oxidation of activated and nonactivated alcohols under mild reaction conditions. The catalyst was characterized by nitrogen adsorption–desorption measurement, thermogravimetric

  发现具有咪唑骨架的周期性介孔有机硅纳米空间内的原位生成的金纳米粒子是高活性，选择性和可重复使用的催化剂，可在温和的反应条件下对活化和非活化醇进行好氧氧化。该催化剂的特征在于氮吸附-解吸测量，热重分析（TGA），透射电子显微镜（TEM），元素分析（EA），漫反射红外傅里叶变换光谱（DRIFT），X射线光电子能谱（XPS）和电感耦合等离子体原子发射光谱法（ICP-AES）。在Cs 2 CO 3（35°C）或K 2的存在下，该催化剂表现出优异的催化活性。一氧化碳3（60°C）作为反应基础在甲苯中作为反应溶剂。在两种反应条件下，各种类型的醇（最多35个实例），包括活化的苄基，伯和仲脂族，杂环和具有挑战性的环状脂族醇，都以良好的产率和选择性很好地转化为预期的羰基化合物。还回收了催化剂并将其再利用至少七个反应循环。来自三个独立浸出测试的数据表明，浸出金颗粒的量可以忽略不计（<0.2 ppm）。据信，桥

表征谱图